diff --git a/src/Sentry/Protocol/Envelopes/Envelope.cs b/src/Sentry/Protocol/Envelopes/Envelope.cs
index 0174dbd32a..edb432dc5b 100644
--- a/src/Sentry/Protocol/Envelopes/Envelope.cs
+++ b/src/Sentry/Protocol/Envelopes/Envelope.cs
@@ -155,8 +155,10 @@ internal async Task SerializeAsync(
         {
             try
             {
-                await item.SerializeAsync(stream, logger, cancellationToken).ConfigureAwait(false);
-                await stream.WriteNewlineAsync(cancellationToken).ConfigureAwait(false);
+                if (await item.SerializeAsync(stream, logger, dropEmptyAttachment: true, cancellationToken).ConfigureAwait(false))
+                {
+                    await stream.WriteNewlineAsync(cancellationToken).ConfigureAwait(false);
+                }
             }
             catch (Exception e)
             {
@@ -180,8 +182,10 @@ internal void Serialize(Stream stream, IDiagnosticLogger? logger, ISystemClock c
         {
             try
             {
-                item.Serialize(stream, logger);
-                stream.WriteNewline();
+                if (item.Serialize(stream, logger, dropEmptyAttachment: true))
+                {
+                    stream.WriteNewline();
+                }
             }
             catch (Exception e)
             {
diff --git a/src/Sentry/Protocol/Envelopes/EnvelopeItem.cs b/src/Sentry/Protocol/Envelopes/EnvelopeItem.cs
index 364d15087e..3b1e84f7a6 100644
--- a/src/Sentry/Protocol/Envelopes/EnvelopeItem.cs
+++ b/src/Sentry/Protocol/Envelopes/EnvelopeItem.cs
@@ -175,7 +175,11 @@ private static void SerializeHeader(
     }
 
     /// <inheritdoc />
-    public async Task SerializeAsync(Stream stream, IDiagnosticLogger? logger,
+    public Task SerializeAsync(Stream stream, IDiagnosticLogger? logger,
+        CancellationToken cancellationToken = default) =>
+        SerializeAsync(stream, logger, dropEmptyAttachment: false, cancellationToken);
+
+    internal async Task<bool> SerializeAsync(Stream stream, IDiagnosticLogger? logger, bool dropEmptyAttachment,
         CancellationToken cancellationToken = default)
     {
         // Always calculate the length of the payload, as Sentry will reject envelopes that have incorrect lengths
@@ -189,6 +193,11 @@ public async Task SerializeAsync(Stream stream, IDiagnosticLogger? logger,
         await using (payloadBuffer.ConfigureAwait(false))
 #endif
         {
+            if (dropEmptyAttachment && IsEmptyAttachmentOfUnknownLength(payloadBuffer, logger))
+            {
+                return false;
+            }
+
             // Write to the outbound stream asynchronously. It's likely either an HttpRequestStream or a FileStream.
 
             // Header
@@ -199,11 +208,15 @@ public async Task SerializeAsync(Stream stream, IDiagnosticLogger? logger,
 
             // Payload
             await payloadBuffer.CopyToAsync(stream, cancellationToken).ConfigureAwait(false);
+            return true;
         }
     }
 
     /// <inheritdoc />
-    public void Serialize(Stream stream, IDiagnosticLogger? logger)
+    public void Serialize(Stream stream, IDiagnosticLogger? logger) =>
+        Serialize(stream, logger, dropEmptyAttachment: false);
+
+    internal bool Serialize(Stream stream, IDiagnosticLogger? logger, bool dropEmptyAttachment)
     {
         // Always calculate the length of the payload, as Sentry will reject envelopes that have incorrect lengths
         // in item headers. Don't trust any previously calculated value to be correct.
@@ -211,6 +224,11 @@ public void Serialize(Stream stream, IDiagnosticLogger? logger)
 
         using var payloadBuffer = BufferPayload(logger);
 
+        if (dropEmptyAttachment && IsEmptyAttachmentOfUnknownLength(payloadBuffer, logger))
+        {
+            return false;
+        }
+
         // Header
         var headerWithLength = Header.ToDict();
         headerWithLength[LengthKey] = payloadBuffer.Length;
@@ -219,6 +237,18 @@ public void Serialize(Stream stream, IDiagnosticLogger? logger)
 
         // Payload
         payloadBuffer.CopyTo(stream);
+        return true;
+    }
+
+    private bool IsEmptyAttachmentOfUnknownLength(MemoryStream payloadBuffer, IDiagnosticLogger? logger)
+    {
+        if (payloadBuffer.Length != 0 || TryGetLength() is not null || Payload is not BufferedStreamSerializable)
+        {
+            return false;
+        }
+
+        logger?.LogWarning("Did not add '{0}' to envelope because the attachment was empty.", TryGetFileName());
+        return true;
     }
 
     /// <inheritdoc />
diff --git a/test/Sentry.Tests/Protocol/Envelopes/AttachmentSerializationTests.cs b/test/Sentry.Tests/Protocol/Envelopes/AttachmentSerializationTests.cs
index 061fdaddca..69b2d7229d 100644
--- a/test/Sentry.Tests/Protocol/Envelopes/AttachmentSerializationTests.cs
+++ b/test/Sentry.Tests/Protocol/Envelopes/AttachmentSerializationTests.cs
@@ -389,4 +389,70 @@ public void FromEvent_EmptyByteAttachment_DoesNotAddAttachment()
             .Should()
             .Be(0);
     }
+
+    [Fact]
+    public async Task Serialization_EmptyNonSeekableStreamAttachment_DropsAttachment()
+    {
+        // Arrange
+        using var envelope = CreateEventEnvelopeWithEmptyNonSeekableAttachment();
+
+        // Act
+        var serialized = await envelope.SerializeToStringAsync(_testOutputLogger, _fakeClock);
+
+        // Assert
+        serialized.Should().NotContain("empty.jpg").And.NotContain("\n\n");
+        using var stream = new MemoryStream(Encoding.UTF8.GetBytes(serialized));
+        using var deserialized = await Envelope.DeserializeAsync(stream);
+        deserialized.Items.Should().ContainSingle()
+            .Which.TryGetType().Should().Be(EnvelopeItem.TypeValueEvent);
+    }
+
+    [Fact]
+    public async Task Serialization_EmptyNonSeekableStreamAttachmentSynchronously_DropsAttachment()
+    {
+        // Arrange
+        using var envelope = CreateEventEnvelopeWithEmptyNonSeekableAttachment();
+
+        // Act
+        var serialized = envelope.SerializeToString(_testOutputLogger, _fakeClock);
+
+        // Assert
+        serialized.Should().NotContain("empty.jpg").And.NotContain("\n\n");
+        using var stream = new MemoryStream(Encoding.UTF8.GetBytes(serialized));
+        using var deserialized = await Envelope.DeserializeAsync(stream);
+        deserialized.Items.Should().ContainSingle()
+            .Which.TryGetType().Should().Be(EnvelopeItem.TypeValueEvent);
+    }
+
+    [Fact]
+    public async Task Serialization_EmptyAttachmentOfKnownLengthAfterRoundTrip_KeepsAttachment()
+    {
+        // Arrange
+        var attachment = new SentryAttachment(
+            AttachmentType.Default,
+            new StreamAttachmentContent(new MemoryStream()),
+            "empty.log",
+            "text/plain");
+        using var envelope = Envelope.FromAttachment(SentryId.Create(), attachment, _testOutputLogger);
+        using var cached = new MemoryStream(Encoding.UTF8.GetBytes(
+            await envelope.SerializeToStringAsync(_testOutputLogger, _fakeClock)));
+        using var deserialized = await Envelope.DeserializeAsync(cached);
+
+        // Act
+        var serialized = await deserialized.SerializeToStringAsync(_testOutputLogger, _fakeClock);
+
+        // Assert
+        serialized.Should().Contain("empty.log");
+    }
+
+    private Envelope CreateEventEnvelopeWithEmptyNonSeekableAttachment()
+    {
+        var attachment = new SentryAttachment(
+            AttachmentType.Default,
+            new StreamAttachmentContent(new NonSeekableReadStream(new MemoryStream())),
+            "empty.jpg",
+            "image/jpeg");
+
+        return Envelope.FromEvent(new SentryEvent(), _testOutputLogger, [attachment]);
+    }
 }